(7S,8aR)-1-acetyl-7-methyl-1,2,3,4,6,7,8,8a-octahydroquinolin-5-yl trifluoromethanesulfonate | 1202394-95-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: (7S,8aR)-1-acetyl-7-methyl-1,2,3,4,6,7,8,8a-octahydroquinolin-5-yl trifluoromethanesulfonate
• 英文别名: [(7S,8aR)-1-acetyl-7-methyl-3,4,6,7,8,8a-hexahydro-2H-quinolin-5-yl] trifluoromethanesulfonate
• CAS: 1202394-95-3
• 化学式: C₁₃H₁₈F₃NO₄S
• 分子量: 341.351
• InChiKey: LUBZNMWVPRHUIM-GZMMTYOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (7S,8aR)-1-acetyl-7-methyl-1,2,3,4,6,7,8,8a-octahydroquinolin-5-yl trifluoromethanesulfonate 生成 (7S,8aS)-1-acetyl-7-methyl-1,2,3,4,6,7,8,8a-octahydroquinolin-5-yl trifluoromethanesulfonate
  参考文献：
  名称：

  Total Synthesis of (−)-Lycoperine A

  摘要：

  Lycoperine A was synthesized through a highly convergent route in which a double alkylation of 2,6-dicyano-N-benzylpiperidine with the octahydroquinoline moiety gave the lycoperine skeleton. The octahydroquinoline was prepared by a desymmetrization reaction of 5-methylcyclohexane-1,3-dione. Hydrolysis, reductive amination, and cyclization gave lycoperine A in 13 steps and 3% overall yield. The absolute configuration of lycoperine A was assigned as 6R,6'R,8R,8'R,13S,17R.

  DOI：

  10.1021/ol902389e
• 作为产物：
  描述：

  N-苯基双(三氟甲烷磺酰)亚胺 、 (4aS,7S,8aR)-1-ethanoyl-7-methyloctahydroquinolin-5(1H)-one 在 potassium tert-butylate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以79%的产率得到(7S,8aR)-1-acetyl-7-methyl-1,2,3,4,6,7,8,8a-octahydroquinolin-5-yl trifluoromethanesulfonate
  参考文献：
  名称：

  Total Synthesis of (−)-Lycoperine A

  摘要：

  Lycoperine A was synthesized through a highly convergent route in which a double alkylation of 2,6-dicyano-N-benzylpiperidine with the octahydroquinoline moiety gave the lycoperine skeleton. The octahydroquinoline was prepared by a desymmetrization reaction of 5-methylcyclohexane-1,3-dione. Hydrolysis, reductive amination, and cyclization gave lycoperine A in 13 steps and 3% overall yield. The absolute configuration of lycoperine A was assigned as 6R,6'R,8R,8'R,13S,17R.

  DOI：

  10.1021/ol902389e